Diisopropylethylamine → HCID 15984410, compound

Participants

Reaction Steps

An ice-cooled mixture of (3S*,5R*)-5-(toluene-4-sulfonylamino)-piperidine-1,3-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester (208.2 mg, 0.4 mmol), O-(1H-6-chlorobenzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (182 mg, 0.44 mmol) and N-ethyldiisopropylamine (27.4 μL, 0.16 mmol) in CH2Cl2/CH3CN 1:1 (3 mL) is stirred for 10 min. After the addition of 2-[2-(4-methoxy-butoxy)-phenyl]-2-phenyl-ethylamine (119.8 mg, 0.4 mmol), the ice-bath is removed and stirring is continued for 14 h at RT. The reaction mixture is distributed between ethyl acetate and 10% K2CO3 solution. The aqueous layer is separated and extracted twice with ethyl acetate. The combined organic layers are dried over Na2SO4 and evaporated in vacuo. The residue is stirred for 1 h with a freshly prepared mixture of CH2Cl2/piperidine 4:1 (5 mL), evaporated and the residue purified by preparative HPLC (C18 column; 10-100% CH3CN+0.1% TFA/H2O+0.1% TFA/20 min, flow 20 mL/min). The combined pure fractions are treated with Na2CO3, CH3CN is removed in vacuo, and the residual aqueous phase is extracted three times with CH2Cl2. The combined organic layers are dried (Na2SO4) and evaporated to afford the title compound as a slightly beige amorphous solid. MS: 580.4 [M+H]+; tR (HPLC, Nucleosil C18; 5-100% CH3CN+0.1% TFA/H2O+0.1% TFA for 8 min, flow 1.5 ml/min): 5.61 min.

Provenance & Evidence